Have you ever looked at a couple you know and wonder how in God’s name did they get together? What on earth could have possessed two people so undeniably different and seemingly incompatible to come together? Well Dash and Lily’s Book of Dares more or less tells the tale as to how such an occurrence can happen. The book alternates perspectives each chapter, with David Levithan writing Dash, and Rachel Cohn writing Lily. The two styles and characters couldn’t be more different if they tried, and watching the two try to find an equal ground was an entertaining and fun read.

Dash, allegedly a 16 year old guy whose music, literature and sarcasm make him read more like a cynical 25 year old who has fallen head first into a vat of existentialism. Think stereotypical Manhattan graduate school elitist and then stick him in high school. It’s ridiculous and slightly grating, but he’s such a snobby book elitist it somehow makes you adore him. Dash is a loner by trade and spends most of his time in and out of a massive New York book store learning new words and reading avant garde books. In his quest to revisit J.D. Salinger books that aren’t Catcher in the Rye, he stumbles across a red notebook filled with clues that lead him on a scavenger hunt throughout the bookstore. It takes him to obscure titles to ones you wouldn’t want to be caught reading in public, and each time he gets a few more letters to answer his riddle. Ultimately upon solving it he realizes it’s a challenge- if he got this far he can leave his name and contact information and the owner of the notebook will be in touch. Dash, being more than slightly pompous, chose to send the notebook owner on her own quest, and so begins the series of dares.

Lily, the owner of the notebook, is about as different to Dash as two people can get. While he is all teenage broodiness she personifies happiness and cheer. He hates Christmas and she runs around wishing everyone, “Happy Eve of the Eve of Christmas Eve!” For the first time, she’s alone on Christmas, as her parents are in Fiji and her grandfather is in Florida, and her brother is far too wrapped up in his new boyfriend to pay her any attention. She’s therefore running around in this false five year old cheer trying to infuse the world with Christmas by starting up caroling groups, baking a billion cookies, and dressing like a Christmas sweater come to life.  She’s childishly naïve and cannot handle things not working out, so much so that her childhood nickname was Shrilly because her voice would hit octaves only dogs could hear. Lily is difficult to like, at least for me; I’m hard pressed to believe you can live in Manhattan through the age of 16 and act like a five year old who has been isolated from society.

However, she is the perfect anecdote to Dash’s cynicism, and throughout the novel she sends him on multiple Christmas-themed escapades, and he forces her to come out of her shell. At some point they begin to resemble people their own age as they both are forced to interact with strangers in scenarios way out of their comfort zones. They also begin to trust the person on the other side of the notebook and realize that perhaps neither of them are quite the outcast they thought they were.

The book is a fun romp through Manhattan, and as it’s written by the same authors’ of Nick and Norah’s Infinite Playlist it has a similar feel and an intrinsic love of New York City. Seeing that the entire story takes place over Christmas break, it’s a perfect book to curl up with on a cold day over the holidays. The characters are unique, the dares and riddles are outlandish, and somehow through it all you can see how two people who are polar opposites somehow make perfect sense together.

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